74936-70-2

Basic information

• Product Name: 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 2-cyanoethyl 1-methylethyl ester
• Synonyms: 1,4-dihydro-2,6-dimethyl-4-(3'-nitrophenyl)-pyridine-3,5-dicarboxylic acid isopropyl 2-cyanoethyl ester;2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-cyano-ethyl) ester 5-isopropyl ester;2-cyanoethyl isopropyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate
• CAS NO: 74936-70-2
• Molecular Formula: C21H23N3O6
• Molecular Weight: 413.43
• Mol File: 74936-70-2.mol

Chemical Properties

• Boiling Point: 584.1±50.0 °C(Predicted)
• Density: 1.244±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 2-cyanoethyl 1-methylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 2-cyanoethyl 1-methylethyl ester(74936-70-2)
• EPA Substance Registry System: 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 2-cyanoethyl 1-methylethyl ester(74936-70-2)

Safety Data

• Hazardous Substances Data: 74936-70-2(Hazardous Substances Data)

Upstream product

• 14205-46-0 isopropyl 3-aminocrotonate 
• 99-61-6 3-nitro-benzaldehyde 
• 65193-87-5 2-cyanoethylacetoacetate 
• 542-08-5 isopropyl acetoacetate 
• 143093-33-8 isopropyl β-aminocrotonate 
• 193539-61-6 (Z)-3-Amino-but-2-enoic acid 2-cyano-ethyl ester 
• 39562-25-9 3-oxo-2-(3-nitrophenylmethylene)butanoic acid isopropyl ester 
• 118431-79-1 2-[(3-nitrophenyl)methylene]-3-oxobutanoic acid,1-methylethyl ester 
• 88977-32-6 2-cyanoethyl 3-amino-2-butenoate 

Downstream Products

• 74936-69-9 1,4-dihydro-2,6-dimethyl-4-(3'-nitrophenyl)-pyridine-3,5-dicarboxylic acid monoisopropyl ester 

Relevant articles and documents

Compound and its as L-type calcium channel blocker or/and application of acetylcholine esterase inhibitors

Disclosed in this invention are compounds and the uses as L-type calcium channel blocker and/or acetylcholinesterase inhibitor thereof. The uses of said compounds in the manufactures of a medicament for the treatment of cardiovascular diseases, apoplexy or senile dementia are also disclosed in the present invention.

Syntheses, calcium channel antagonist and anticonvulsant activities of substituted 1,4-dihydro-3,5-pyridinedicarboxylates containing various 3-alkyl ester substituents

A group of 3-alkyl-5-isopropyl 4-aryl-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylates 10-20 containing an amine, quaternary ammonium, aryl(heteroaryl)alkenyl, 4-(4-fluorophenyl)-piperazin-1-yl or methoxy moiety in the C-3 alkyl ester R-substituent in combination with a C-4 phenyl ring bearing a 2,3-Cl2, 3-NO2, 3-NMe2, 4-NMe2 or 3,4,5-(OMe)3 X-substituent were prepared using the Hantzsch 1,4-dihydropyridine reaction. In vitro calcium channel antagonist activity (CCA) was determined using a guinea pig ileum longitudinal smooth muscle assay. In the C-4 3-nitrophenyl series of compounds, the C-3 ester R substituent was a determinant CCA activity where the relative potency order was -CH2CH2CH=C-(2-methylphenyl)2 ≤ -CH2CH2NMe2.HCl > -CH2CH2CH=C (3-methyl-2-thienyl)2 > -CH2CH2+NMe3I-. The position and nature of the C-4 phenyl X-substituent, were also determinants of CCA activity where the relative activity order was 3-NMe2>4-NMe2>3,4,5-(OMe)3. Anticonvulsant activities were determined in mice using the subcutaneous metrazol (scMet) and maximal electroshock (MES) screens. The compounds investigated were generally not effective for protecting against scMet induced seizures, except for 10 {X = 2,3-Cl2, R = 2-[4-(4-fluorophenyl)piperazin-1-yl]ethyl} and 14a (X = 3-NMe2.HCl, R = CH2CH2OMe), which exhibited modest activity. Compound 11a (X = 3-NO2, R = -CH2CH2NMe2.HCl) was the most effective agent in the MES screen. All of the compounds investigated, except for 11b (X = 3-NO2, R = -CH2CH2+NMe3 I-, Kp = 0.15) are lipophilic with n-octanol/aqueous phosphate buffer (pH = 7.4) partition coefficients (Kp) in the 121-424 range relative to the reference drug nimodipine (Kp = 187). The structure-activity relationship acquired reinforce the concept that calcium is only one of several factors that are involved in seizure generation.

Mild and facile cleavage of 2-cyanoethyl ester using sodium sulfide or tetrabutylammonium fluoride. Synthesis of 1,4-dihydropyridine monocarboxylic acids and unsymmetrical 1,4-dihydropyridine dicarboxylates

Several 3-(2-cyanoethyl)-1,4-dihydropyridine carboxylates (16) were prepared in moderate to good yields by means of the Hantzsch reaction. Treatment of these carboxylates with a weak base such as sodium sulfide or tetrabutylammonium fluoride at room temperature afforded smoothly the corresponding 1,4-dihydropyridine monocarboxylic acids (18) in good yields. The monocarboxylic acids 18n and 18o were esterified with 2-nitrooxypropanol or N-(2-hydroxyethyl)nicotinamide p-toluenesulfonic acid salt to afford the selective coronary vasodilators CD-349 (5) and CD-832 (6), respectively.

Synthesis and antihypertensive activities of new 1,4-dihydropyridine derivatives containing a nitrooxy moiety at the 3-ester position

The synthesis of a new series of dihydropyridines containing a nitrooxy moiety at the 3-ester position is described. The antihypertensive activity of the compounds was examined and compared with that of nifedipine; some of them were relatively potent. The structure-activity relationship is also discussed.

Nimodipine: Synthesis and metabolic pathway

Key step of the synthesis of the calcium antagonistic cerebral vasodilator (±) isopropyl-2-methoxyethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (Bay e 9736, nimodipine) is the cyclising Michael addition. A pharmacokinetic study with 14C-nimodipine in the rat revealed as major metabolites the dihydropyridines as well as the pyridines. A potential metabolic pathway is discussed involving ether cleavage and oxidation to the pyridine form as primary biotransformation steps. Reference metabolites were synthesized using 1,4-dihydropyridines with appropriate functionalities as precursors.